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This chapter considers the geopolitical context into which Henry C. C. Astwood was born. Centering Astwood’s birth land, the Turks Islands, it examines the British Caribbean’s transition from slavery to free labor in the 1830s. It then pushes forward to the 1860s, demonstrating how the emancipation era’s debate over Black civic capacity linked the Dominican War of Restoration (1863–65), the US Civil War (1861–65), the Morant Bay Rebellion (1865), and other contemporaneous events. Turks islanders like Astwood kept close tabs on these affairs. This chapter shows how Turks islanders suffered setbacks from the US war and assisted Dominicans in their war against Spain. It also argues that white Turks islanders’ ideas about the Dominican Republic and Haiti shifted after the events at Morant Bay. Last, the chapter reveals the historical, economic, social, and familial ties that Black and mixed-race Turks islanders, especially the Astwood family, held to Hispaniola’s northern coast.

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